3-Bromoquinoline → HCID 19697782, compound

Participants

Reaction Steps

26,0 g of 3-bromoquinoline and 4.35 g of 2-oxazolidinone in 200 ml of xylene are heated under reflux in the presence of 7.4 g of potassium acetate and 4.8 g of copper powder for 9 h, analogously to the process of B.Renger in Synthesis (1985) 856. After the mixture has been worked up, the crude product is purified over silica gel with a 500:10:1 mixture of methylene chloride, methanol and concentrated ammonia as the mobile phase, to give 3-(quinolin-3-yl)-2-oxazolidinone as a crystalline solid: Rf (500:10:1 mixture of methylene chloride, methanol and concentrated ammonia)=0.39; FAB-MS: (M+H)+ =215. Hydrogenation of 0.67 g of the resulting product in 10 ml of ethanol in the presence of 0.1 g of palladium-on-charcoal (10% of palladium) at 50° C. in the course of 20 h and FC over 80 g of silica get (mobile phase N) gives 3(R,S)-(2-oxo-oxazolidin-3-yl)-1,2,3,4-tetrahydroquinoline as a white solid: Rf (N)=0.61; MS: M+ =218.

Provenance & Evidence